“The Look On Her Face Was Priceless”: 24 Of The Most Horrible Dates Witnessed By Restaurant Staff

Had a customer who was meeting a guy for a blind date. I saw a man walk in the room, scan the room, and walk out. After a couple lonely glasses of wine, and constant checking of the phone, it became apparent that he bailed. I asked if she wanted to order a meal and she declined. I gave her a dessert and told her the bill had been taken care of.

I was the female half of several dates where the guy just did an extensive monologue throughout the whole thing. You wonder if you are going to get lockjaw from trying to smile politely. This happened in my 20s and happened in my 70s - those kind of guys don’t change. 100 years from now it will still be the same.

Had a girl I went on with the night before come into the restaurant I was working at the next night on a different date & sat in my section 💀 She did not know I worked there. The look on her face was priceless when I said “Hey folks, my name is Ben & I’ll be taking care of you tonight.” 😂.

Former waiter here. The sheer number of dates I saw that were just one person going on and on and on about themselves and not asking the other person there a *single* question was mind-blowing.

But I think the worst one I ever saw was when a guy asked the person he was with to quickly run lines with him for an audition he wanted to do. I think he thought it was some kind of flex, like he would be impressing his date by slipping in his amazing acting skills before their food arrived.

Not surprisingly, perhaps, his acting skills were not so amazing. And then he said "what did you think?!" and instead of waiting for the answer, started explaining the brilliance behind some of his acting choices while his date was forced to half-heartedly nod along and praise the performance. It was so painfully awkward.

Funniest :
Guy was on his phone the entire meal name dropping like crazy. When dessert cane he finally hung up and said oh sorry I was just on a really important call with Mark Wahlberg. For the next 15ish mins, his date pretended not to know who that is while he became more and more desperate to make sure she knew he was a big deal. He named like 30 movies, he sang some marky mark, he even said his brother was a new kid on the block. This absolute queen just kept going yeah no sorry not ringing any bells. New kids on the what? Who is Martin Scorsese, is he new?

Saddest :
I worked for a while at a kosher restaurant that catered to a very ultra traditional crowd. I saw a lot of first meetings for arranged marriages. The one that stuck out the most was this guy who spent the whole date criticizing her while she sat silently and avoided eye contact. He ate a full meal but would only allow her to have water. Their families sat at the next table and nobody spoke up for her. I wanted to flip their table over, it was so horrible to watch. I hope they didn’t get married.

I remember this one time a couple were on their first date, the restaurant was empty, and the guy was a regular, so I made sure that they had a great experience. Hooked them up with a free app and some wine, let the lady play her music on the speakers. When I was bringing them dessert, she got a phone call and she was told that her father had died. It went from a near perfect evening to probably the worst night of her life.

I might accidentally be someone else’s story. My boyfriend and I went out to celebrate out first anniversary of dating. We thought it’d be fun to dress fancy, so we definitely stood out a bit.

While we’re waiting for the bill, the conversation turns to acting techniques. BF says that the best way to portray anger isn’t to make a stock “angry” face, but to let your face go completely slack.

I give it a try, and apparently give BF the most withering look - right as the waiter comes up behind him with the bill.

The poor guy did a complete 180 and basically hid behind the bar for several minutes while I died laughing.

I’m not a waiter, but the couple at the next table was on what was clearly a first date. I was facing the same direction as she was so i couldn’t see her face, but i could see his and could hear everything he said.

And when i say I could hear everything HE said, i mean i don’t even know what her voice sounded like because the guy literally wouldn’t shut up. I don’t think she said a single word the entire date. He just talked AT her nonstop for a solid hour. Didn’t ask her a single question. Didn’t pause to even eat his food, just talked while chewing. I cannot even imagine what was going through her brain while this was going on….

We had this one older lady come in every week. She wore a different wig every time. Should would ask to sit at the same exact table and ask that we would act like we’ve never met her before. Then, throughout the day, sometimes the entire day, she would have multiple dates. These men would just fawn all over her. If they did not bring her flowers, it was a wrap. She would ask that we help sneak her out of the restaurant until the guy left. Sometimes it got real awkward. She never paid. She also asked that we only address her as Tiger.

It was weird.

I saw many good dates, bad dates and everything in between. The saddest was a couple that seemed like a good match. Lady was so excited but the guy was insecure but successful. Persian dude in early thirties. He got there early and it was a great date spot. I chatted with him while he nursed a drink to cool the nerves. He was a very down to earth guy and i felt like we genuinely connected. 


She shows up and was so excited... until he talked about himself and his career for the next 90 minutes. I wanted to scream at the guy to ask a question but he was trying to impress her and was a totally different guy.

Busboy at a really nice restaurant. Middle aged couple sitting at a two top on an outside patio. Across from them was a boisterous group of 6, who were throwing money around. Bought a bottle of Dom Perignon for the couple to apologize for being so loud, as they left. Apparently, the husband brought his wife to the restaurant to be in a public place to tell her he’d had an affair. Telling her this over the champagne. She blows up, as you’d expect. Loudly berates him and starts asking about what occurred sexually between him and the other woman. All the wait staff walked by at 0.5 speed and convened in the bar to share what they heard.

I've seen a bunch but the best was when a guy brought in a canned Pepsi and just asked for a glass with ice. He then offered one to his date.


It did not go well. .

Had a table where the guy ordered a ton of food, and when the bill came, he started making excuses about how he 'forgot his wallet' and couldn’t pay. The girl was mortified, especially since she had already paid for her own meal. She looked like she was ready to crawl under the table.

I have 2 stories, both of which I've witnessed myself.

First off, sat in a Thai restaurant in the trafford centre with my wife, and there's a table with a young couple there. She was 18 or 19, he was about the same age. The conversation seemed somewhat forced as HIS MUM WAS WITH HIM, saying nothing with a face like thunder. And when he went to the toilet, she followed him. When they'd left her alone, she just sat there texting disconsolately.

Second, at a Chinese restaurant in Oxford. Again, a young couple sat next to us, but he spoke incessantly about how well traveled he was. I don't think I heard a single word out of her at all, it wasn't a conversation, he was just subjecting her to a monologue. He spoke at length about how he'd visited Third World Village and lived there for a month. (Didn't name the village or country, didn't say A third world village, he made it sound like a theme park. Said he'd eaten a dog while there. Said he had experience teaching underprivileged children as he'd taught in some of the worst schools on the isle of wight. For anyone unfamiliar with the isle of Wight it's very affluent, very pretty and rural. I imagine that the roughest schools there have slightly tatty wisteria, and serve inferior caviar at lunch.

Poor girls.

So, not a waiter but am sure we’re some waiter’s story. OH and I are sitting in a restaurant after dropping our son off at university to start his first term. I’m feeling all the feelings - happy for him, of course but also so so sad. We order and I start crying. OH holds my hand but I just cry some more. He squeezes my hand and says ‘sweetheart, you need to stop crying because people are thinking it’s me.’ Sure enough, lots of angry eyes on OH who they likely presume is breaking up with me or admitting some peccadillo or other. We laugh about it often, ten years on. Still miss my baby boy. 😂.

Not date but breakup!!

I had a couple that would come in almost weekly, for like over a year , always mega nice and generous tippers and then one day they were both at the table, not saying much, with the young lady tears streaming down her face and the young man with an incredibly solemn thousand yard stare and inknew they were breaking up… but my question was like why would you do this at the restaurant of your nice memories?? Or in public at all?? .

When I was in college I was working in a bar where the man left his phone in his jacket, and left the jacket on the chair when he went to the bathroom. His girlfriend/wife immediately went for it, and within the minute and 45 seconds he was gone she apparently found what she was looking for and as he returned she started yelling and flipped the high top table over. She ran out with his phone and he ran after and we just comped the check because no one was interrupting that.
Edited to add: I hope it was a scam, they deserved every single bite for free, but they didn’t stay long enough to enjoy the fruits of their performance if so. Also I watched all the color drain from that man’s face and he looked like a fish swallowed a golf ball, so an epic performance if it was staged.

Not a waiter, I was just eating with family when I was about 14 or something. The section of my table didn't have anyone opposite as my parents sat next to me and there was this couple 18-20ish who seemed to be on a date.

The guy seemed to be trying to talk to her, but she would not put down her phone. Just texting constantly, talking a picture of the dish. Every now and then, she'd wave her hand like "Sorry, just sending a quick message" set down her phone for all of 30 seconds before picking it back up and messaging again.

I remember she excused herself to the toilet, the guy looked around the place and saw me looking at him. He half-shrugged his shoulders like "can you believe this?" I could only shrug in agreement. I think he finished his food quickly and ended the date soon after that, she hadn't even touched her food yet.

As one of the closers, if anyone came in between 9-930 no big deal but I’d make it obvious we were closing at 10pm.
Anyone in after 930pm I’d tell them kitchen closed in 15 mins and after 940 I’d just tell everyone it was to go only, the managers didn’t like this, but I’m the first to greet the people and I’m doing all the work and that last hour; I’m the Captain now vibes lol.
So a nicely dressed guy comes in at 845 asks for a table for two, declines anything but water til his date arrives. I did what I could to stay busy but after 45 mins and now it being 30 mins to close, I approached and warned him the kitchen closes in 15 and he said his person was walking in. A woman in yoga clothes, walks up and flips down opposite him; never looking up from her phone.
He ends up having to order for both of them because she’s not present beyond physically being at the table. I get the order in and as I’m passing to another table I hear him quietly pleading she give him a chance - at what idk I was pushing some old folks outta my party booth and didn’t hear. Their food comes up and as I’m dropping it off she says “it’s just not the way I thought it’d be, so I don’t want to do it anymore.” And his face was crushed, body language said he was flatlining.
I automatically bring boxes with the check, and as she hadn’t touched her food I wanted to save time. I pretty much knew, dessert wasn’t gonna happen but the manager was out front and I had to try that final upsell or be banished to the back section with the flickering lightbulb.
“Just ask if they want dessert, just ask if they want dessert!” I said it the whole way to their table and with a giant smile on my face I asked “so guys, you thinking about DIVORCE TONIGHT?!” cue my horrified gasp and the girl just looks up at me from her phone and says “see Justin? Even the waitress knows this isn’t working.” And poor Justin just looked at me as I literally tossed the checkbook and boxes and said “I’m so sorry.. Jesus!” The manager gave them a discount and I never again offered dessert.

Not a waiter, but I did once see a woman storm out of a date in a very nice restaurant. The couple was seated at an adjacent table to me. She got up abruptly and left, just before the food was served.

The waiters seemed to handle it very discreetly: they brought a cover to keep her meal warm in case she returned, and after a generous interval, quietly took her plate away. The guy waited for a while before forlornly eating his own meal and asking for the bill.